136265-10-6Relevant articles and documents
Atomically precise palladium nanocluster catalyzed tandem oxidation processes of alcohols and phosphorous ylides: Facile access to α,β-unsaturated esters
Gao, Taiping,Du, Jialei,Liu, Wenyan,Ren, Mingxia
, (2020)
The mesoporous silica nanosphere supported palladium nanocluster was synthesized through a simple impregnation method and well characterized. The as prepared catalyst shows excellent catalytic performance in tandem oxidation process (TOP) of alcohol and phosphorous ylide, which provides an efficient access to α,β-unsaturated esters with high yields utilizes 1 atmosphere of molecular oxygen as sole oxidant. This work represents the first example of atomically precise palladium nanocluster catalyzed tandem oxidation process of alcohol and phosphorous ylide and is expected to open new horizons for nanoclusters in the tandem reactions.
Synthesis and in vitro evaluation of antimycobacterial and cytotoxic activity of new α,β-unsaturated amide, oxazoline and oxazole derivatives from L-serine
Aguirre-Rentería, Saúl A.,Arredondo-Espinoza, Eder,Avalos-Alanís, Francisco G.,Carrizales-Castillo, Juan J. J.,Garza-González, Elvira,Hernández-Fernández, Eugenio,Rivas-Galindo, Verónica M.,del Rayo Camacho Corona, María
, (2020)
The synthesis of 19 compounds derived from L-serine and analogs of p-substituted cinnamic acid is reported. Oxazolines 9 and oxazoles 10 have high antitubercular activity with Minimum Inhibitory Concentration (MIC) of 0.7812–25.0 μg/mL (3.21–100.3 μM), against two strains of Mycobacterium tuberculosis sensitive to first-line drugs Isoniazid (INH), Rifampicin (RIF), Ethambutol (EMB), Pyrazinamide (PZE) (H37Rv) and a clinical isolate resistant to INH, RIF and EMB (G122). The cytotoxic evaluation shows that oxazoles have low activity, finding viability>96% against the VERO cell line. The results show these compounds could be considered as future alternatives for antitubercular treatment.
Quantitative Structure-Property Relationship (QSPR) models for a local quantum descriptor: Investigation of the 4- and 3-substituted-cinnamic acid esterification
Rodrigues-Santos, Cláudio E.,Echevarria, Aurea,Sant'Anna, Carlos M.R.,Bitencourt, Thiago B.,Nascimento, Maria G.,Bauerfeldt, Glauco F.
, p. 17493 - 17510 (2015)
In this work, the theoretical description of the 4- and 3-substituted-cinnamic acid esterification with different electron donating and electron withdrawing groups was performed at the B3LYP and M06-2X levels, as a two-step process: the O-protonation and the nucleophile attack by ethanol. In parallel, an experimental work devoted to the synthesis and characterization of the substituted-cinnamate esters has also been performed. In order to quantify the substituents effects, quantitative structure-property relationship (QSPR) models based on the atomic charges, Fukui functions and the Frontier Effective-for-Reaction Molecular Orbitals (FERMO) energies were investigated. In fact, the Fukui functions, f+C and f-O, indicated poor correlations for each individual step, and in contrast with the general literature, the O-protonation step is affected both by the FERMO energies and the O-charges of the carbonyl group. Since the process was shown to not be totally described by either charge- or frontier-orbitals, it is proposed to be frontier-charge-miscere controlled. Moreover, the observed trend for the experimental reaction yields suggests that the electron withdrawing groups favor the reaction and the same was observed for Step 2, which can thus be pointed out as the determining step.
Identification of (6S)-cyclopropyl-6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamines as new HBV capsid assembly modulators
Lv, Kai,Wu, Shuo,Tao, Zeyu,Wang, Aoyu,Xu, Shijie,Yang, Lu,Gao, Qiang,Wang, Apeng,Qin, Xiaoyu,Jiang, Bin,Wu, Wenhao,Jia, Xuedong,Li, Yuhuan,Jiang, Jiandong,Liu, Mingliang
supporting information, (2021/11/16)
GYH2-18 is a type II HBV CAM with 6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamine (DPPC) skeleton discovered by Roche INC. A series of GYH2-18 derivatives were designed, synthesized and evaluated for their anti-HBV activity. Two compounds 2f and 3k exhibited excellent anti-HBV activity, low cytotoxicity and accepted oral PK profiles. Chiral separation of 2f and 3k was conducted successfully, and (6S)-cyclopropyl DPPC isomers 2f-1, 2f-3, 3k-1 and 3k-3 were identified to be much more active than the corresponding (6R)-ones. The preliminary structure-activity relationship, particle gel assay and molecular modeling studies were also discussed, which provide useful indications for guiding the further rational design of new (6S)-cyclopropyl DPPC analogues.
Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents
Ramavath, Vijayalakshmi,Rupanawar, Bapurao D.,More, Satish G.,Bansode, Ajay H.,Suryavanshi, Gurunath
, p. 8806 - 8813 (2021/05/26)
We have developed hypervalent iodine(iii) induced oxidative olefination of primary and secondary benzylamines using 2C-Wittig reagents, which provides easy access to α,β-unsaturated esters. Mild reaction conditions, good to excellent yields with high (E) selectivity, and a broad substrate scope are the key features of this reaction. We have successfully carried out the gram-scale synthesis of α,β-unsaturated esters.
